Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopen...

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Autores principales: Kojima, Taiki, Obata, Rika, Saito, Tsuyoshi, Einaga, Yasuaki, Nishiyama, Shigeru
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4361996/
https://www.ncbi.nlm.nih.gov/pubmed/25815070
http://dx.doi.org/10.3762/bjoc.11.21
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author Kojima, Taiki
Obata, Rika
Saito, Tsuyoshi
Einaga, Yasuaki
Nishiyama, Shigeru
author_facet Kojima, Taiki
Obata, Rika
Saito, Tsuyoshi
Einaga, Yasuaki
Nishiyama, Shigeru
author_sort Kojima, Taiki
collection PubMed
description The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.
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spelling pubmed-43619962015-03-26 Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products Kojima, Taiki Obata, Rika Saito, Tsuyoshi Einaga, Yasuaki Nishiyama, Shigeru Beilstein J Org Chem Letter The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer. Beilstein-Institut 2015-02-03 /pmc/articles/PMC4361996/ /pubmed/25815070 http://dx.doi.org/10.3762/bjoc.11.21 Text en Copyright © 2015, Kojima et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Kojima, Taiki
Obata, Rika
Saito, Tsuyoshi
Einaga, Yasuaki
Nishiyama, Shigeru
Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title_full Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title_fullStr Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title_full_unstemmed Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title_short Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
title_sort cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4361996/
https://www.ncbi.nlm.nih.gov/pubmed/25815070
http://dx.doi.org/10.3762/bjoc.11.21
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